Preparation of nicotine ionic liquids and their application to catalytic synthesis of phenyl-substituted cyclic carbonate

To expand processing of tobacco and develop new application of nicotine, the bromide, tetrafluoroborate and hexafluorophosphate of butylnicotine were prepared. Their structures were characterized by FT-IR, HRMS and ¹H NMR, and their application to the catalytic synthesis of phenyl-substituted cyclic carbonate was investigated. The results showed that:1) The prepared bromide, tetrafluoroborate and hexafluorophosphate of butylnicotine had the general features of ionic liquids. 2) The application of butylnicotine bromide was the best for this purpose. After styrene oxide and CO₂(1 MPa) reacted at 100℃ for 6 h in this ionic liquid, the yield of cyclic carbonate reached more than 95%. With tert-butyl hydroperoxide (TBHP) as oxidant and sodium phosphotungstate as co-catalyst, styrene reacted with CO₂ (1 MPa) under gradient conditions of 60℃/3 h and 100℃/24 h, the yield of cyclic carbonate was above 75%. 3) The butylnicotine bromide ionic liquid could be reclaimed easily and be recycled at least 6 times with the yield of cyclic carbonates no less than 87% and 65% under the above two processing conditions. This study shows that developing nicotine-derived ionic liquid is beneficial to the production of phenyl cyclic carbonate and has the potential to reduce greenhouse effect.